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Showing Compound 8-HETE (FDB023400)

Record Information
Version1.0
Creation date2011-09-21 00:29:22 UTC
Update date2015-07-21 06:57:41 UTC
Primary IDFDB023400
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8-HETE
Description8(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes. (PMID: 7592593, 9113987) [HMDB]
CAS Number98462-03-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(5Z,8S,9e,11Z,14Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoateGenerator
(5Z,8S,9e,11Z,14Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acidChEBI
(5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoatehmdb
(5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acidhmdb
(5Z,9e,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoateGenerator
(5Z,9e,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acidChEBI
(5Z,9e,11Z,14Z)-(8S)-8-Hydroxyicosa-5,9,11,14-tetraenoateGenerator
(5Z,9e,11Z,14Z)-(8S)-8-Hydroxyicosa-5,9,11,14-tetraenoic acidChEBI
(8S)-Hydroxy-(5Z),(9e),(11Z),(14Z)-eicosatetraenoateGenerator
(8S)-Hydroxy-(5Z),(9e),(11Z),(14Z)-eicosatetraenoic acidChEBI
(S)-(Z,e,Z,Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoateGenerator
(S)-(Z,e,Z,Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acidChEBI
8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoatehmdb
8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoic acidhmdb
8(S)-HydroxyeicosatetraenoateGenerator
8(S)-Hydroxyeicosatetraenoic acidChEBI
8S-HETEhmdb
8S-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoatehmdb
8S-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP5.87ALOGPS
logP5.36ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability39.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O3
IUPAC name(8S,9E)-8-hydroxyicosa-5,9,11,14-tetraenoic acid
InChI IdentifierInChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6?,10-9?,14-11?,16-13+/t19-/m1/s1
InChI KeyNLUNAYAEIJYXRB-XVZCTOAFSA-N
Isomeric SMILES[H][C@](O)(CC=CCCCC(O)=O)\C=C\C=CCC=CCCCCC
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
Classification
Description Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4446278
ChEMBL IDNot Available
KEGG Compound IDC14776
Pubchem Compound ID5283154
Pubchem Substance IDNot Available
ChEBI ID34486
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04679
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference